My Situationships Never Last — So I Asked My “Exes” What Went Wrong

I’ve been doing some self-reflection and examination. Truthfully, I’ve never been in a real relationship. Rom coms are my least favorite film genre because they’re fairy tales of unobtainable fantasies. He’s not actually going to chase you down the street holding a bouquet of flowers just to say he was sorry. Come on!

But, I’ve also never had the chance to see if this scenario was even a possibility. I’ve crushed and dated, but that’s about it. There’s no “boyfriends” in my history, just some browsing situations.

And lately, my single friends have been dropping like flies. Everyone is boo’d up except for me. No need to extend the plus one on an invite because everyone knows I’m rolling solo. I don’t even have spares to accompany me in a pinch. For some reason, I have yet to bask in the ambience of love.

So, as I started to wonder where things went wrong, or if they went wrong at all, I did a scary thing. I asked some of these “situationships” why we never went any further.

Let’s be clear, this wasn’t an impulsive decision, I’d been thinking about asking them for quite some time. Watching people’s lives progress via social media can stir up a lot of “what if” feelings for even the most stoic person. So, I decided to dive into my little black book, which is actually more of a flyer, and reach out to a few of these guys.

1. We were totally clueless

“Young and dumb” is a phrase that is used often for a variety of situations. In my case, it was the official answer from the first guy. At first, I was taken aback. The answer irritated me. I needed details. I wanted to know every thought and action that contributed to our demise before we even really got started. Yes, I was being very dramatic.

But it was almost as if he had asked the same question to himself before. There was no hesitation in his reply, like he had considered all possible answers and came to the conclusion that he was just young and dumb.

While digesting his response, I started to think back to the time we were kickin’ it. I thought about what I was into, what my priorities were and how I chose to spend a lot of my time. And I also realized it: we were both young and dumb.

I was equally complicit in this ignorance that eventually led to a mutual decision of just being acquaintances. I didn’t know what a relationship was nor how to cultivate one. MTV’s Real World wasn’t exactly an ideal depiction of how real relationships happen.

Neither of us were really ready. It was only in seeing what we’ve each grown into that we realized how naive we actually were. As the saying goes, “hindsight is 20/20.”

2. Making them guess what I want

“You never said you wanted more.” I had to eat that one. I spend a lot of time encouraging others to communicate their needs, so it’s a shame my past self ignored my own advice.

Dropping hints and being subtle only got me so far. After a while, the tactic got to be kind of annoying. Sarcastic comments and sharp tongue responses created a distaste for one another. We began to act on the words never spoken. They filled the space between us and eventually pushed us so far apart we never found our way back.

You can’t really get what you need or want without communicating your desires. The expectation that he would “figure it out” was never met. And sure, I could’ve helped, but let’s face it: I was immature. I didn’t really understand the value of using my words. I thought being coy was the way to go.

I was wrong. Lack of communication is miscommunication and the result is another lesson learned.

3. “She’s out of my league”

It’s very rare that a guy will admit to insecurity. I definitely wasn’t expecting it, not from this guy. He’s extremely confident, strong, sometimes pushing on arrogant, and speaks with conviction. Imagine my surprise when I found out the reason we never became an official couple is because he thought I would get bored with him.

At the time, I was finishing my degree and had a lot going on personally. There was a lot of juggling of events and projects. From an outsider’s perspective, my life would probably have been considered somewhat hectic. I was always on the phone or sending an email. I was busy. He was great — patient and understanding, or so I thought.

Truthfully, he was intimidated by what he considered “success” at that time — college degree, working in my chosen field, paying bills on time (sometimes early). In his mind, I had it going on at a level that he didn’t think he could reach. (I know — I’m still in shock.)

Did he say anything back then? No. He just slowly phased himself out. We hung out less and less until we didn’t see each other much at all.

Caution: this isn’t for the faint of heart. Fortunately for me, the guys I asked were gentlemen when it came to giving me honest feedback. I didn’t need the tissues I strategically placed next to my phone while waiting for their responses but it definitely could’ve gone another way.

If you’re considering going the High Fidelity route towards self-reflection, here’s a few things to remember.

1. Is your torch still burning for any of these people?

This process can be very vulnerable. It’s important to make sure that your desire to seek the truth doesn’t damage an already tender heart, especially if things didn’t end on good terms.

Check your meter before reaching out. Think about how things ended and decide if this is a door you’d like to go through. I had already worked through my feelings for the guys I chose to reach out to, but if I hadn’t, the process would have undoubtedly been more difficult.

2. Am I ready for their truth?

Be prepared for their version of events. You may find yourself remembering their series of events differently, and that’s okay. You may have thought something you did was sweet and sincere and they may have viewed it as manipulative and vindictive, and that’s okay.

They’re entitled to their perspective of the relationship and you need to brace yourself for the fact that your histories may not align perfectly.

3. Who they say you are is not who you are

At the end of all this, I had to separate myself from who they viewed me as and who I actually am. It’s great to have a mini exit-interview to get another person’s insight on how you show up in the world but, at the end of the day, you have to know who you are and keep a firm grasp on that.

Don’t let what you find out shake your identity, leaving you sprawled out like fallen Jenga blocks. You can have a few misses and still be an amazing person.

Let’s be real here — we’ve all spent way too much time overthinking a situation only to find out that it wasn’t that serious. Over the years, I’ve become an emotional bag lady, holding on to these situationships as if they were something to be ashamed of or another failure on my list of bad choices.

But at any given moment, there are countless factors at work in someone’s personal life that result in a number of behaviors.

That’s my biggest takeaway in this exercise of bravery in talking to my past: it wasn’t personal. At all. Both parties had to own the part we played. We had to share custody of the situationship. It was our responsibility to share our needs, communicate our wants, and make the decision to keep it going or call it quits.

In the end, none of these men held anything against me, so why hold it against myself? I appreciate the honesty and bravery of these guys. I’m sure my question initially gave them a brief moment of shock. Although we didn’t work our way from situationship to an official relationship, I’m still glad they’re a part of my story.

Kit Stone is a writer and digital content creator based in the Bay Area covering entertainment, pop culture, wellness, family, and other topics. Connect with her on Instagram or Twitter.